At a minimum, they could have listed a 15 to 30 day vacancy gap for turnover and repairs.Chicago is FOR SURE A CHALLENGING CITY TO BE A PROPERTY MANAGER, but likely even more than other industries, you get what you pay for with a property manager. 

Nine month into my low paying job in a new city, I had no savings.

Always threatening to call a lawyer or the city. 

A good investor agent can find deals for you, you can cold call, drive around, and scour city data.

I heard of developers doing this with farm land around cities.

Examples:44109 (median home price went from roughly 50k to 125k in 8 years)https://www.zillow.com/home-values/77009/cleveland-oh-44109/ 44102 (median home price went from roughly 30k to 120k in 8 years)https://www.zillow.com/home-values/77002/cleveland-oh-44102/ 44106 (median home price went from roughly 100k to 200k in 8 years)https://www.zillow.com/home-values/77006/cleveland-oh-44106/ It has the highest rents on average in all of Ohio for major cities and the median home value is not even in the top 3.

Kansas City has a strong medical presence so traveling medical professionals are always needing a place to stay.

I am trying to determine whether these cities are good markets to invest in.

Originally, I was hoping to have the property owner hold the property while I take the agricultural property through the feasibility study and rezoning to have paper lots approved by the city I choose to annex the property into.    

You don't need to move or work in another city.